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Product Name | 3-Indoleacrylic acid |
Cas Number | 1721-35-7 |
Formula | C11H9NO2 |
Molar Mass | 187.20 g/mol |
Melting Point | 153-155°C |
Boiling Point | Not available |
Density | Not available |
Solubility In Water | Slightly soluble |
Appearance | White to off-white powder |
Odor | Characteristically indolic |
Pka | 4.6 |
Usage | Research chemical, potential pharmaceutical intermediate |
Safety Hazards | Irritant, handle with care |
What is the chemical structure of 3-Indoleacrylic acid?
3 - Indoleacrylic acid is an organic compound with a distinct chemical structure.3 - Indoleacrylic Acid is an organic compound that has a distinct chemistry.
At its core, 3 - Indoleacrylic acid contains an indole ring system.In its core, 3 – Indoleacrylic Acid contains an indole-ring system. The indole ring consists of a benzene ring fused to a pyrrole ring.The indole is made up of a benzene and pyrrole ring. The benzene ring is a six - membered aromatic ring with alternating double bonds, which confers high stability due to resonance.The benzene is a six-membered aromatic ring, with double bonds that alternate. This gives it a high degree of stability due to resonance. The pyrrole ring is a five - membered heterocyclic ring containing a nitrogen atom.The pyrrole is a five-membered heterocyclic chain containing a nitrogen. This nitrogen atom has a lone pair of electrons that contributes to the aromaticity of the indole ring through resonance.This nitrogen atom is a lone electron pair that contributes to aromaticity in the indole rings through resonance.
Attached to the indole ring at the 3 - position is an acrylic acid moiety.The acrylic acid moiety is attached to the indole at the 3 – position. The acrylic acid part has a structure of CH2=CH - COOH.The acrylic acid portion has a structure CH2=CH-COOH. The double bond in the acrylic acid group is an important feature as it can participate in various chemical reactions such as addition reactions.The double bond of the acrylic acid group can be used in many chemical reactions, such as addition reactions. For example, it can react with electrophiles, where the p - electrons of the double bond are attracted to electron - deficient species.It can, for example, react with electrophiles where the p-electrons of the double bonds are attracted to species that lack electrons.
The carboxylic acid group (-COOH) at the end of the acrylic acid chain is also very reactive.The carboxylic group (-COOH), at the end of acrylic acid chain, is also very reactive. It can undergo acid - base reactions, acting as a proton donor in the presence of a base.It can undergo acid-base reactions, acting as an proton donor when a base is present. It can form salts with metal hydroxides or amines.It can form salts when combined with metal hydroxides and amines. Additionally, the carboxylic acid group can participate in esterification reactions, where it reacts with alcohols in the presence of an acid catalyst to form esters.The carboxylic group can also participate in esterification reactions where it reacts alcohols in presence of an acid catalyser to form esters.
The overall structure of 3 - Indoleacrylic acid combines the unique reactivity and stability characteristics of the indole ring with those of the acrylic acid functional group.The overall structure of 3- Indoleacrylic Acid combines the unique reactivity, stability and reactivity of the indole rings with those of acrylic acid functional groups. This makes 3 - Indoleacrylic acid useful in various fields.This makes 3 – Indoleacrylic Acid useful in many fields. In the pharmaceutical industry, the indole ring and the acrylic acid moiety together may contribute to its biological activity, potentially acting as a lead compound for the development of drugs.In the pharmaceutical industry the indole moiety and the acrylic acid ring together may contribute to the biological activity of the compound, potentially acting as lead compounds for the development drugs. In the chemical synthesis field, its multiple reactive sites allow for the creation of more complex organic molecules through a series of chemical reactions.In the field of chemical synthesis, its multiple reactive site allows for the creation of complex organic molecules by a series chemical reactions. The double bond can be used for polymerization reactions in some cases, while the carboxylic acid group can be modified to introduce different functional groups.In some cases, the double bond can be utilized for polymerization reactions. The carboxylic acid can also be modified to introduce other functional groups. Overall, the chemical structure of 3 - Indoleacrylic acid provides a rich platform for both natural and synthetic chemistry applications.Overall, the chemical composition of 3 - Indoleacrylic Acid provides a rich platform both for natural and synthetic chemistry.
What are the applications of 3-Indoleacrylic acid?
3 - Indoleacrylic acid has several important applications in different fields.Indoleacrylic acid is used in many different fields.
In the agricultural sector, it serves as a plant growth regulator.In the agricultural industry, it is used as a plant growth regulator. It can enhance plant growth and development in multiple ways.It can be used to enhance plant growth in many ways. For instance, it promotes root development. Stronger roots are better at absorbing water and nutrients from the soil, which is crucial for the overall health and vigor of the plant.Stronger roots can better absorb water and nutrients in the soil. This is important for the overall health of the plant. This, in turn, can lead to increased crop yields.This can increase crop yields. It also influences processes like cell elongation and division in plants.It can also influence processes such as cell division and elongation in plants. By regulating these fundamental cellular activities, it helps plants reach their full growth potential.By regulating the fundamental cellular functions, it helps plants achieve their full potential. Moreover, 3 - indoleacrylic acid can enhance a plant's resistance to various environmental stresses such as drought, salinity, and extreme temperatures.Moreover, 3 indoleacrylic acids can increase a plant's ability to resist environmental stresses like drought, salinity and extreme temperatures. This is because it can trigger certain physiological and biochemical changes in the plant that enable it to better cope with adverse conditions.This is because the acid can trigger certain biochemical and physiological changes in the plant, which enable it to better deal with adverse conditions.
In the pharmaceutical industry, 3 - indoleacrylic acid has shown potential biological activities.In the pharmaceutical industry 3 - indoleacrylic has shown potential biological activity. It has been investigated for its anti - inflammatory properties.Its anti-inflammatory properties have been studied. Inflammation is a key factor in many diseases, including arthritis and some cardiovascular diseases.Inflammation plays a major role in many diseases including arthritis and certain cardiovascular diseases. Compounds with anti - inflammatory effects can help in reducing pain and swelling associated with these conditions.Compounds that have anti-inflammatory effects can reduce the pain and swelling caused by these conditions. Additionally, it may have anti - tumor activities.It may also have anti-tumor activities. Research is ongoing to understand how it can interact with cancer cells, potentially inhibiting their growth, inducing apoptosis (programmed cell death), or interfering with the tumor's blood vessel formation.It is being studied to see how it interacts with cancer cells. It may inhibit their growth, induce apoptosis, or interfere with the formation of blood vessels in the tumor. These properties make it a promising candidate for the development of new drugs to combat cancer and other inflammatory - related disorders.These properties make it an attractive candidate for the development new drugs to fight cancer and other inflammatory-related disorders.
In the field of organic synthesis, 3 - indoleacrylic acid is a valuable intermediate.In the field organic synthesis, 3-indoleacrylic is a valuable intermediary. It can be used as a starting material to synthesize a wide range of more complex organic compounds.It can be used to synthesize many more complex organic compounds. Chemists can modify its structure through various chemical reactions to create molecules with specific properties.Chemists are able to modify its structure by using different chemical reactions in order to create molecules that have specific properties. These synthesized compounds can then be used in different applications, from the production of fine chemicals to the development of new materials with unique physical and chemical characteristics.These compounds can be used for a variety of applications, including the production of fine chemicals and the development of new materials.
Overall, 3 - indoleacrylic acid's diverse applications in agriculture, pharmaceuticals, and organic synthesis make it a compound of great interest and importance in these respective fields.Overall, 3 – indoleacrylic acids diverse applications in agriculture and pharmaceuticals, as well as organic synthesis, make it an important compound in these respective fields. Its potential continues to be explored, and further research may uncover even more beneficial uses in the future.Further research could uncover even more uses for this compound.
How is 3-Indoleacrylic acid synthesized?
3 - Indoleacrylic acid can be synthesized through several methods.Three different methods are available to synthesize indoleacrylic acid. One common approach is via the Knoevenagel condensation reaction.Knoevenagel condensation is a common method.
In this method, indole - 3 - aldehyde and malonic acid are used as starting materials.This method uses malonic acid and indole-3-aldehyde as starting materials. The reaction is typically carried out in the presence of a base catalyst.The reaction is usually carried out with a catalyst. Pyridine is often used as the base and also as a solvent in many cases.In many cases, pyridine is used both as a base and as a solvent.
The reaction mechanism begins with the deprotonation of malonic acid by the base.The reaction begins with the deprotonation by the base of malonic acid. The resulting enolate anion then attacks the carbonyl carbon of indole - 3 - aldehyde.The enolate anion that results attacks the carbonyl atom of indole-3-aldehyde. This forms an intermediate.This intermediate is formed. Subsequently, a dehydration step occurs, facilitated by the basic conditions.The basic conditions facilitate a subsequent dehydration step. The carboxylic acid group of the intermediate loses a water molecule, and the double bond is formed, leading to the formation of 3 - indoleacrylic acid.The carboxylic group of the intermediate loses one water molecule and the double bond forms, leading to 3 - indoleacrylic acids. The by - product of this reaction is carbon dioxide, which is released during the dehydration step.This reaction produces carbon dioxide which is released in the dehydration process.
Another synthetic route involves the use of indole and acrylonitrile.Indole and Acrylonitrile are used in a second synthetic route. First, indole reacts with acrylonitrile in the presence of a suitable catalyst, such as a metal - based catalyst.Indole is first reacted with acrylonitrile using a suitable catalyst such as a metal-based catalyst. This reaction leads to the formation of an intermediate with a cyanoethyl group attached to the indole.This reaction results in the formation of a intermediate with an attached cyanoethyl. Then, through hydrolysis of the cyano group in the presence of an acid or a base, the cyano group is converted into a carboxylic acid group, resulting in 3 - indoleacrylic acid.The cyano group can be converted to a carboxylic group by hydrolyzing it in the presence of an alkali or base. This results in 3 -indoleacrylic acids.
The acid - catalyzed hydrolysis might involve using sulfuric acid or hydrochloric acid, while the base - catalyzed hydrolysis could use sodium hydroxide or potassium hydroxide.Acid-catalyzed hydrogenation could involve the use of hydrochloric or sulfuric acids, while base-catalyzed hydrogenation could use sodium or potassium hydroxide. The choice of hydrolysis method depends on various factors such as the reaction conditions, the availability of reagents, and the ease of product isolation.The choice of hydrolysis depends on a number of factors, including the reaction conditions, availability of reagents and ease of product separation.
After the synthesis, the product may need to be purified.Purification may be required after the synthesis. Common purification methods include recrystallization, where the crude product is dissolved in a suitable solvent (such as ethanol or a mixture of solvents) at an elevated temperature and then allowed to cool slowly.Recrystallization is one of the most common purification methods. The crude product is dissolved at a high temperature in a solvent (such ethanol or a combination of solvents), and then allowed to slowly cool. This causes the 3 - indoleacrylic acid to crystallize out, leaving impurities in the solution.This causes the 3 – indoleacrylic to crystallize, leaving the impurities in solution. Column chromatography can also be used for purification, especially when the product contains closely related impurities.The column chromatography method can be used to purify a product, especially if it contains impurities that are closely related. Here, the mixture is passed through a column filled with a stationary phase, and different components elute at different rates, allowing for the separation and isolation of pure 3 - indoleacrylic acid.The mixture is passed over a column containing a stationary phase. Different components elute in different rates. This allows for the separation and isolation 3 -indoleacrylic acids.
What are the physical properties of 3-Indoleacrylic acid?
3 - Indoleacrylic acid, also known as indole - 3 - acrylic acid, has several distinct physical properties.The 3 - Indoleacrylic Acid, also known by the name indole 3 – acrylic acid, has distinct physical properties.
Appearance: It typically exists as a white to light - yellow crystalline solid.Appearance: It is typically a white or light-yellow crystalline solid. This solid form is a result of the intermolecular forces present in the compound.This solid form is the result of intermolecular forces in the compound. The arrangement of molecules in a regular, repeating pattern gives rise to the crystalline structure, which is characteristic of many organic solids.The crystalline structure of many organic compounds is a result of the arrangement of molecules into a regular and repeating pattern.
Melting Point: The melting point of 3 - indoleacrylic acid is around 185 - 187 degC.Melting Point: 3 - Indoleacrylic Acid melts at 185-187 degC. This relatively high melting point can be attributed to the strength of the intermolecular forces within the crystal lattice.This high melting point is due to the strong intermolecular forces in the crystal lattice. The presence of hydrogen bonding, van der Waals forces, and potentially p - p stacking interactions between the indole rings contribute to holding the molecules tightly together.Hydrogen bonding, van der waals forces, and possibly p-p stacking interactions between indole rings all contribute to keeping the molecules together. To overcome these forces and transition from the solid to the liquid state, a significant amount of energy in the form of heat is required, resulting in a relatively high melting temperature.To overcome these forces, and transition from the liquid to the solid state, a large amount of energy is required in the form heat, resulting in an extremely high melting temperature.
Solubility: In terms of solubility, 3 - indoleacrylic acid shows limited solubility in water.Solubility: 3 - Indoleacrylic Acid is not very soluble in water. This is because the molecule has a relatively large non - polar indole ring and a hydrophobic carbon - chain segment (the acrylic acid part to some extent).This is due to the fact that the molecule contains a relatively large indole ring, and a hydrophobic segment of carbon - chain (to a certain extent, the acrylic acid part). Non - polar substances tend to be insoluble or sparingly soluble in polar solvents like water due to the principle of "like dissolves like."Due to the principle "like dissolves alike", non-polar substances are insoluble or only sparingly solubilized in polar solvents such as water. However, it is more soluble in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).It is more soluble in organic solutions such as ethanol (methanol), dimethyl sulfoxide, and DMSO. These organic solvents have a greater ability to interact with the non - polar regions of 3 - indoleacrylic acid through van der Waals forces and potentially other weak intermolecular interactions, allowing the compound to dissolve.These organic solvents interact more readily with the non-polar regions of the 3 - indoleacrylic acids through van der Waals interactions and possibly other weak intermolecular interaction, allowing it to dissolve.
Density: While the exact density values may vary depending on factors such as purity and measurement conditions, it has a density that is typical for an organic solid.Density: Although the exact density values can vary depending on factors like purity and measurement conditions it has a typical density for an organic solid. Density is related to the mass of the molecules and how closely they are packed in the solid state.The density is determined by the mass of molecules and the way they are packed together in the solid state. The density is influenced by the molecular structure, with the relatively compact arrangement of atoms in the indole and acrylic acid moieties contributing to its overall density characteristics.The molecular structure influences the density. The relatively compact arrangement of the atoms within the acrylic acid and indole moieties contributes to the overall density characteristics.
Optical Properties: 3 - indoleacrylic acid may exhibit certain optical properties.Optical Properties 3 - Indoleacrylic Acid may exhibit certain optical characteristics. The indole ring contains a conjugated system of double bonds, which can absorb light in the ultraviolet - visible region.The indole rings contain a conjugated double bond system that can absorb light in both the ultraviolet and visible regions. This conjugated system allows for the excitation of electrons upon absorption of photons of appropriate wavelengths, leading to characteristic absorption bands in the UV - Vis spectrum.This conjugated system allows the excitation electrons when photons with appropriate wavelengths are absorbed, leading to characteristic bands of absorption in the UV- Vis spectrum. These optical properties can be used for analytical purposes, such as identifying the compound or determining its concentration in a sample using spectroscopic techniques.These optical properties are useful for analytical purposes such as identifying a compound or determining the concentration of a sample by using spectroscopic methods.
What are the potential risks and safety precautions associated with 3-Indoleacrylic acid?
3 - Indoleacrylic acid is a chemical compound with certain potential risks and corresponding safety precautions.3 - Indoleacrylic Acid is a chemical compound that carries certain risks and safety precautions.
Potential Risks
1. Health - related risksHealth-related risks
Inhalation risks: If 3 - Indoleacrylic acid is present in the form of dust or fine particles in the air, inhalation may cause irritation to the respiratory tract.Inhalation: 3 - Indoleacrylic Acid can cause irritation of the respiratory tract if it is present as dust or fine particles. This can lead to symptoms such as coughing, shortness of breath, and in more severe cases, it might exacerbate pre - existing respiratory conditions like asthma.This can cause symptoms like coughing and shortness of breathe, or in more severe cases it may exacerbate respiratory conditions such as asthma.
Skin contact risks: Direct contact with the skin can result in skin irritation.Direct skin contact can cause irritation. It may cause redness, itching, and in some individuals, allergic reactions.It can cause skin irritation, such as redness, itching and allergic reactions in some people. Prolonged or repeated skin exposure could potentially lead to more serious dermatological issues.Repeated or prolonged skin exposure can lead to more serious skin issues.
Eye contact risks: Getting 3 - Indoleacrylic acid in the eyes is extremely dangerous.Eye contact risks: 3 - Indoleacrylic Acid in the eyes can be extremely dangerous. It can cause intense irritation, pain, and may even damage the cornea, which could have long - term consequences for vision.It can cause intense pain, irritation, and even damage to the cornea. This could have long-term effects on vision.
Ingestion risks: Ingesting 3 - Indoleacrylic acid can be harmful.Ingestion risks: 3 - Indoleacrylic Acid can be harmful. It may lead to irritation of the gastrointestinal tract, resulting in symptoms like nausea, vomiting, abdominal pain, and diarrhea.It can cause irritation of the gastrointestinal system, which may result in symptoms such as nausea, vomiting and abdominal pain. In severe cases, it could potentially damage internal organs.In severe cases, internal organs could be damaged.
2. Environmental risks
If 3 - Indoleacrylic acid is released into the environment, it may have an impact on aquatic life.If 3 - Indoleacrylic Acid is released into the water, it could have an impact on aquatic animals. It could potentially be toxic to fish, invertebrates, and other organisms in water bodies.It could be toxic to fish and other organisms living in water bodies. Additionally, in soil, it might affect soil microorganisms, which play a crucial role in nutrient cycling and plant health.In soil, it could also affect soil microorganisms that are crucial to nutrient cycling and the health of plants.
Safety Precautions
1. Personal protective equipment (PPE)Personal protective equipment (PPE),
When handling 3 - Indoleacrylic acid, it is essential to wear appropriate PPE.Wearing appropriate PPE is essential when handling 3 - Indoleacrylic Acid. This includes safety goggles to protect the eyes from any splashes or airborne particles.Safety goggles are recommended to protect your eyes from airborne particles or splashes. Gloves, preferably made of materials like nitrile or neoprene, should be worn to prevent skin contact.Gloves made from nitrile, neoprene or other materials that prevent skin contact should be worn. A lab coat or protective clothing should be donned to cover the body and prevent any chemical from coming into contact with the skin or clothing.Wearing a lab coat or protective clothing will cover the entire body and prevent chemicals from coming in contact with clothing or skin.
2. Handling and storageHandling and storage
It should be handled in a well - ventilated area, such as a fume hood, to minimize the risk of inhalation.To minimize the risk of inhalation, it should be handled under a well-ventilated area, such a fume hood. When storing 3 - Indoleacrylic acid, it should be kept in a cool, dry place, away from sources of heat and ignition.Store 3 - Indoleacrylic Acid in a cool and dry place away from heat sources and ignition. The container should be tightly sealed to prevent the release of dust or vapors.The container must be tightly sealed in order to prevent dust or vapors from escaping.
3. Emergency procedures3.
In case of skin contact, immediately wash the affected area with plenty of soap and water for at least 15 minutes.If skin contact occurs, wash the affected area immediately with lots of soap and plenty of water for a minimum of 15 minutes. If eye contact occurs, flush the eyes with copious amounts of water for a minimum of 15 minutes and seek immediate medical attention.If eye contact occurs flush the eyes for at least 15 minutes with plenty of water and seek immediate medical assistance. In case of ingestion, do not induce vomiting unless directed by a medical professional, and seek emergency medical help promptly.In the event of ingestion, you should not induce vomiting without the permission of a medical professional. Seek immediate medical attention. If there is an inhalation incident, move to fresh air immediately and seek medical advice if symptoms persist.In the event of an inhalation, you should move to fresh air as soon as possible and seek medical advice immediately if symptoms persist.